A Short, General Access to Folded, all-cis-Azatetraquinane Ring Systems

Mehta, Goverdhan; Prabhakar, C.

doi:10.1021/jo00119a048

Cited by 22 publications

(4 citation statements)

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“…In 1995, triquinane 111 was treated with phenylhydrazine to generate the mono-hydrazone, which was subsequently subjected to an acid-catalyzed Fischer indolization sequence to generate indolotriquinane 113 (mono-indole). 32 However, twenty years later, in 2015, when the conditions for the Fischer indolization were changed to a deep eutectic mixture of dimethyl urea and tartaric acid, a twofold cyclization was observed and symmetrical diindole derivative 112 was obtained (Scheme 23 ). 33…”

Section: Reagent-based Selectivitymentioning

confidence: 99%

Selectivity: A Goal for Synthetic Economy

Kotha¹,

Ansari²,

Gupta³

2022

Synlett

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Chemical reactivity plays a major role in understanding several aspects of selectivity. Therefore, we present a plethora of reactions that demonstrate our efforts in exploiting interesting cases of selectivity observed in the past three decades. Among them, chemoselectivity, regioselectivity and steroselectivity are discussed. Strain, steric factors, and separations of the reacting functionalities are displayed as prominent features in generating selectivity.

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Section: Reagent-based Selectivitymentioning

confidence: 99%

Selectivity: A Goal for Synthetic Economy

Kotha¹,

Ansari²,

Gupta³

2022

Synlett

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“…Once 7 , 10 , and 11 had been prepared as representatives of compounds with unsaturated moieties at C 1 and carrying the amidinohydrazone at C 5 , we decided to obtain the nitrogen derivative at C 10 . The hydroxy derivative 4 was converted into the aminomethyl derivative via PCC oxidation followed by reductive amination, although this methodology produces the desired compound in low yields, as described in the literature. Another possibility for introducing a nitrogenated function replacing the hydroxyl groups is the Mitsunobu reaction. , This procedure allows the transformation of the hydroxyl group into the amino group in good overall yield .…”

Section: Chemistrymentioning

confidence: 99%

Inotropic Activity of Hydroindene Amidinohydrazones

et al. 2001

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Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na(+),K(+)-ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human alpha2beta1 isozyme (associated with the inotropic effect) with respect to the alpha1beta1 isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

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“…To install the alkane chain connecting the two nitrogen atoms, we plan to use alkylation with allylbromide followed by RCM and hydrogenation protocols. It is known that a mono-indole derivative was obtained via Fischer indolization starting with dione 2 and two equivalents of phenylhydrazine hydrochloride, but the diindole derivative 8 [ 58 ] was not obtained under these conditions. Our experience with Fischer indolization of 1 using the low melting mixture protocol gave unusual results as compared with conventional Fischer indolization conditions.…”

Section: Introductionmentioning

confidence: 99%